2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde → HCID 17932557, compound

HRID 1017575

Reaction equation

HRID 1017575 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:24])[NH:13][C:14](=[O:23])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=2)=[CH:3]1.[CH3:25][C:26]1([CH3:33])[O:30][CH:29]([CH:31]=O)[CH2:28][O:27]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:24])[NH:13][C:14](=[O:23])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][CH2:31][CH:29]3[CH2:28][O:27][C:26]([CH3:33])([CH3:25])[O:30]3)[CH:17]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 1107022,2-Dimethyl-1,3-dioxolane-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 5327711Iron oxide, spent

Product 1

HCID 17932557HCID 17932557, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(1-methylindol-3-yl)-4-(3-aminophenyl)-1H-pyrrole-2,5-dione (100 mg, 0.32 mmol) and 2,2-dimethyldioxolane-4-carboxaldehyde (0.38 mmol) (prepared as described in Kumont, von R., et al. Helv. Chim. Acta., 66, 814, (1983)) in dichloromethane (12 mL) was stirred at room temperature for 10 min., and then Na(OAc)3BH (120 mg, 0.57 mmol) was added. The reaction mixture was stirred overnight and then partition between EtOAc and H20. The organic layer was separated, washed with water and concentrated. The crude product was purified by preparatory TLC with 3/1 hexanes/EtOAc to give 3-(1-methylindol-3-yl)-4-[3-(2,2-dimethyldioxolan-4-ylmethylamino)phenyl]-1H-pyrrole-2,5-dione (32.6 mg, 24%).

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. custompartition between EtOAc and H20
  3. customThe organic layer was separated
  4. washwashed with water
  5. concentrationconcentrated
  6. customThe crude product was purified by preparatory TLC with 3/1 hexanes/EtOAc

Sources & evidence

ORD record
ord-bb4da6f1b1944bd3b2902e2850851aa2
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Linked notes

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